Triethylamine → 3-{4-[2-(4-Benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester

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Reaction Steps

2-Ethoxy-3-{4-[2-(4-hydroxyphenyl)ethoxy]phenyl}propanoic acid ethyl ester (described in Example 26b) (0.36 g; 1.0 mmol) was dissolved in dry dichloromethane (25 ml) and benzylisocyanate (0.20 g; 0.185 ml; 1.5 mmol) was added followed by addition of triethylamine (0.22 ml; 1.5 mmol). The solution was stirred at room temperature for 3 hours. The dichloromethane phase was washed with diluted acid, sodium hydrogen carbonate and brine, dried with sodium sulfate and evaporated to give 0.4 g (81%) of crude 3-{4-[2-(4-benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester. The crude material was purified on preparative reversed phase HPLC using a gradient of acetonitrile-water-ammonium acetate as mobile phase. Fractions containing pure product were pooled and the acetonitrile removed in vacuum. The residue was dissolved in dichloromethane, washed with water, dried with sodium sulfate and evaporated to give 0.23 g (48%) of pure 3-{4-[2-(4-benzylcarbamoyloxyphenyl)ethoxy]phenyl}-2-ethoxypropanoic acid ethyl ester

Provenance & Evidence